Condensation is definitely a concern in colder weather. If you create a thermal break that isn't properly sealed against air leakage, warm air from the house will seep behind the walls, bringing lots and lots of moisture with it. Meanwhile the bricks, which are now insulated, are going to be very very cold, and when warm air gets cold it lets go of its moisture - and thus we get condensation.
That condensation would then get trapped inside the walls - and long before you have a problem with brick deterioration you're going to have mold issues that lead to health issues.
The best thing to do to prevent this is to insulate with a substance that also serves as a vapor barrier, which will prevent any air (and thus any moisture) from leaking into the closed cavity. The best product for this IMO is spray foam insulation, because it fills in all the nooks and crannies and IS the vapor barrier.
Alternatively, you could use fiberglass and cover it over with plastic to form a vapor barrier, and this can work IF you properly seal it all the way around the edges, seams and any holes that occur.
Either approach, however, is going to require you to sacrifice living space, as for a proper thermal break you're going to probably want at least 4" of insulation.
Now - with regard to insulating your spare rooms. Don't insulate your interior walls. Put proper insulation in the external walls of those rooms, so that they don't lose heat to the outside. Yes you will be heating them, but if they're properly insulated they're not going to cost much to heat and there are numerous other concerns with turning an inside room into a "cold" room - it's a finished space, after all, and you don't want to risk damaging that by letting it be freezing cold in there.
Since you are in zone 4, R-38 is a reasonable insulation level. That doesn't tell us how much an issue a lack of vapor barrier is. It is less of an issue in dry climates. What a barrier does for you is prevent moisture from condensing inside the insulation, significantly reducing it's insulating value. Ever notice how hypothermia victims have invariably gotten themselves wet? Unfortunately, properly installing one can be very difficult (read: expensive). As it happens, plywood acts somewhat as a barrier, depending on it's construction. Thus, you may need to just focus on gaps and openings.
Another possible make-do vapor barrier is a good heavy coating of latex paint on the ceiling. You may already have this! Truth be told, the best way to insulate would be to remove the plywood and blow in the needed insulation. This gets sealed around all the joists and other ins and outs nicely and makes effective use of what little insulation is already there. However, it may not be worth the effort.
You can still get a good insulation job by layering it on top as you suggest. The draw back is the dead space under the plywood effectively becomes part of your conditioned space, greatly diminishing the value of what's there. Even a plaster ceiling alone is worth something. And you've increased the top story volume you're heating 5-6%. Another issue with this approach is the plywood becomes your vapor barrier. What are the ramifications of moisture condensing on the under side? There's poor air circulation, so it will not dry easily. It could be the cause of a mold colony gaining a foothold, which can have serious health consequences. Or it may not be an issue if you're in a dry climate.
Whichever way you go, try to ensure what ever passes as a vapor barrier is a complete as possible. Ensure any recessed light fixtures are not insulated over, and that no insulation contacts the cans. It may seem more efficient to cover them, but you greatly increase the chance of them overheating and starting a fire. Insulation is little good if your house burns down! A truly efficient ceiling has no recessed light fixtures for this very reason. Note that there are supposedly fixtures rated to be covered, but I don't think I've ever seen one.
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As for sheep's wool it is a great insulating product. I actually ran into 50 rolls at a local Habitat store that had them going for $4 a piece. So I bought them all. They were non-faced rolls and have to be one of the most pleasant insulation experiences of my life.
However you have two problems and neither of them have to do with cleaning. First you must be able to compress the wool so that it stays together and its density is appropriate. I found that it was a lot like rockwool except not itchy. Second the burlap bags are probably a no-no because you would have to prove out their fireproof qualities.
I would talk to local inspector on both. Sure he will be happy with wool but may express his own concerns on top of mine.
And just an FYI. I have no idea where I would order these wool rolls. I have never seen them at any store so obviously someone ordered them special and decided not to use them and gave them to the Habitat store. Also you may want to visit some wool insulation company sites for tips. I don't know what if anything they use to get the wool in firm strips.